期刊
ORGANIC LETTERS
卷 23, 期 24, 页码 9526-9532出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03745
关键词
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资金
- Natural Science Foundation of Zhejiang Province [LQ20B020005]
- Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang [2019R01005]
- Joint Fund of Zhejiang Provincial Natural Science Foundation [LTZ21B020001]
A TfOH-promoted method for synthesizing fluorinated poly-fused heterocycles has been developed, allowing the convenient construction of fluorinated benzofuro[3,2-b]pyridines, 5H-indeno-[1,2-b]pyridines, and 5,6-dihydrobenzo[h]quinolines. This method involves a one-pot [4 + 2] approach and is highlighted by the successful synthesis of three fluoro analogues of bioactive molecules.
A TfOH-promoted synthesis of fluorinated poly-fused heterocycles via the cascade cyclization of azadienes and difluoroenoxysilanes has been developed, leading to the facile construction of fluorinated benzofuro[3,2-b]pyridines, 5H-indeno-[1,2-b]pyridines, and 5,6-dihydrobenzo[h]quinolines. This one-pot formal [4 + 2] approach involves 1,4-difluoroalkylation, desulfo-nylation, cyclization, and dehydrated and dehydrofluorinated aromatization and represents the first application of difluoroenoxysilane in cascade transformations. Furthermore, this methodology is highlighted by the synthesis of three fluoro analogues of bioactive molecules with potent topoisomerase inhibitory activities.
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